| Identification | More | [Name]
L(+)-Diethyl L-tartrate | [CAS]
87-91-2 | [Synonyms]
(2R,3R)-(+)-DIETHYL TARTRATE
(2R,3R)(+)-DIHYDROXYBUTANE-1,4-DIOIC ACID DIETHYL ESTER
DET
(+)-DIETHYL1-2,3-DIHYDROXYSUCCINATE
(+)-DIETHYL-2,3-DIHYDROXYSUCCINATE
(+)-DIETHYL L-TARTRATE
DIETHYL L-(+)-TARTRATE
DIETHYL L-TARTRATE
DIETHYL-L-TARTRATE, (+)-
DIETHYL TARTRATE
FEMA 2378
L-DET
L(+)-DIETHYL L-TARTRATE
L(+)-DIETHYL TARTRATE
L-(+)-TARTARIC ACID DIETHYL ESTER
(+)-TARTARIC ACID DIETHYL ESTER
(R(R*,R*))-2,3-dihydroxy-butanedioicaciddiethylester
2,3-Dihydronxybutanedioicaciddiethylester
2,3-dihydroxy-[theta-(theta,theta)]-butanedioicacidiethylester
Butanedioic acid, 2,3-dihydroxy-[R-(R*,R*)]-, diethyl ester | [EINECS(EC#)]
201-783-3 | [Molecular Formula]
C8H14O6 | [MDL Number]
MFCD00009143 | [Molecular Weight]
206.19 | [MOL File]
87-91-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to light yellow liqui | [Melting point ]
17 °C
| [alpha ]
7.5 º (neat) | [Boiling point ]
280 °C (lit.) | [density ]
1.204 g/mL at 25 °C(lit.)
| [vapor pressure ]
0.402Pa at 25℃ | [FEMA ]
2378 | [refractive index ]
n20/D 1.446(lit.)
| [Fp ]
200 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Water (Slightly) | [form ]
Viscous Liquid | [pka]
11.61±0.20(Predicted) | [color ]
Clear | [Odor]
at 100.00 %. mild fruity wine caramellic | [biological source]
synthetic | [Odor Type]
fruity | [Optical Rotation]
[α]20/D +8.5°, neat | [Water Solubility ]
insoluble | [JECFA Number]
622 | [Merck ]
14,3855 | [BRN ]
1727145 | [Dielectric constant]
4.5（20℃） | [Major Application]
flavors and fragrances | [InChI]
1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m1/s1 | [InChIKey]
YSAVZVORKRDODB-PHDIDXHHSA-N | [SMILES]
CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC | [LogP]
0.2 at 25℃ | [CAS DataBase Reference]
87-91-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Diethyl tartrate(87-91-2) | [EPA Substance Registry System]
87-91-2(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H227 | [Precautionary statements ]
P210e-P280a-P370+P378a-P403+P235-P501a | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29181300 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
D(-)-Tartaric acid-->DL-Tartaric acid-->Diethyl DL-tartrate-->Ethanol-->L(+)-Tartaric acid | [Preparation Products]
(+)-DIOP-->(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol-->N,N,N',N'-Tetramethyl-L-tartramide-->1,3-Dioxolane-4,5-dicarboxylic acid, 2-(2-phenylethenyl)-, diethyl ester, [4R-[2α(E),4α,5β]]- (9CI)-->1,4-Butanedione, 2,3-dihydroxy-1,4-di-1-pyrrolidinyl-, (2R,3R)--->3-diMethoxysuccinate |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to light yellow liqui | [Chemical Properties]
Diethyl tartrate has a mild, fruity, wine aroma.
| [Occurrence]
The d-isomer has not been reported found in nature; the l-isomer and the racemic form are of little importance.
Reported found in sherry, white and red wine. | [Uses]
Diethyl L-(+)-Tartrate is used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke thera
py. | [General Description]
Made from natural tartaric acid | [Flammability and Explosibility]
Nonflammable | [Synthesis]
(1) 30 g of L-(+)-tartaric acid was added to a 500 mL three-necked flask followed by 150 mL of anhydrous ethanol. The stirrer was turned on to make the mixture homogeneously mixed, and the reaction temperature was controlled in the range of 0 to 30 °C. 95.4 g of thionyl chloride was slowly added dropwise for 1.5 h, taking care to control the rate of dropwise acceleration to manage the exothermic process. After the dropwise addition, the reaction system was warmed up to 50 °C and the reaction was continued for 2 hours. After completion of the reaction, ethanol was removed by distillation under reduced pressure to obtain the crude product of diethyl L-(+)-tartarate. (2) To the above crude product, 3.3 g of potassium bicarbonate was added, the temperature was raised to 20 °C and the reaction was stirred for 3 hours. At the end of the reaction, the solid insoluble matter was removed by filtration to obtain 39.6 g of L-(+)-diethyl L-tartrate, and the product was a colorless or light yellow oily liquid with a molar yield of 96.2%. The purity of the product was tested to be 99.4%. | [References]
[1] Tetrahedron Letters, 2013, vol. 54, # 36, p. 4851 - 4853
[2] RSC Advances, 2015, vol. 5, # 15, p. 11687 - 11696
[3] Patent: CN107337603, 2017, A. Location in patent: Paragraph 0025; 0026; 0027; 0028; 0029; 0030; 0031-0040
[4] Journal of Organic Chemistry, 2012, vol. 77, # 19, p. 8465 - 8479,15
[5] Patent: CN106966943, 2017, A. Location in patent: Paragraph 0090; 0091 |
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